Frank (played by Robert Duvall) is a gruff and solitary man, living alone in a small apartment in a rundown Florida town. He spends most of his days walking the streets or sitting in the park, reminiscing about his past as a sailor. One day he meets Walter (played by Richard Harris), a friendly Cuban barber who recently moved to the town and also spends time in the park. Despite their initial differences and occasional clashes, the two men develop an unlikely bond over their shared sense of loneliness and loss.
Frank and Walter start spending more time together, fishing, drinking, and talking about life and love. Frank is intrigued by Walter's stories of Cuba, and gradually opens up about his own painful experiences, including the death of his wife and estrangement from his daughter. Walter, in turn, confides about his own struggles with aging and illness. Their friendship becomes a lifeline for both men as they face the challenges of their old age together.
However, their relationship is tested when Frank meets Elaine (played by Sandra Bullock), a young waitress who befriends him and becomes a surrogate daughter figure. Walter, who has his own complicated feelings about Elaine, feels threatened by her presence and the dynamic between the three of them becomes increasingly tense. Eventually, Frank's behavior towards Elaine becomes inappropriate and she breaks off contact with him. This leads to a rift between Frank and Walter, and they part ways.
As the film ends, both men are once again alone, but with a newfound appreciation for the importance of human connection. They reflect on their time together and the memories they shared, and come to a bittersweet realization that they have been "wrestling Ernest Hemingway," a metaphor for grappling with the tough realities of life and aging, and finding solace in the bonds of friendship.